From hydrolytically labile to hydrolytically stable RuII–arene anticancer complexes with carbohydrate-derived co-ligands

Designing organometallic compounds for catalysis and therapy

“…O,O-ligands have been used to prevent arene-Ru complexes from hydrolysing in RAPTA analogs derivatised with a sugar-bearing phosphate ligand and a biscarboxylate as chelator (77). 170 The Ru-P bond appears to stabilise the O,Ocomplex by accepting electron density. These compounds do not hydrolyse and do not exhibit significant reactivity towards biomolecules.…”

Influence of the π-coordinated arene on the anticancer activity of ruthenium(II) carbohydrate organometallic complexes

“…In recent years, we have reported the development of phosphorus-substituted sugar derivatives with the aim to exploit the enhanced glucose uptake in tumors due to increased glycolytic activity in cancer cells (Berger et al, 2008; Hanif et al, 2010a, 2011, 2012a,b; Nazarov et al, 2012). These organometallic compounds exhibit selective cytotoxicity in tumorigenic cell lines, and dichlorido(η 6 - p -cymene)(3,5,6-bicyclophosphite-1,2- O -cyclohexylidene-α-D-glucofuranoside)ruthenium(II) 1b was found to be more cytotoxic than RAPTA-C in in vitro assays (Berger et al, 2008).…”

“…The carbohydrate compounds are prone to hydrolysis, and they undergo aquation of the first halido ligand in aqueous solution, followed by hydrolysis of a P–O bond of the phosphite ligand, and finally formation of dinuclear species (Berger et al, 2008). The aquation can be hindered or suppressed by replacing ruthenium with osmium and chlorido ligands with dicarboxylates (Hanif et al, 2010a, 2011). …”

Synthesis, characterization and cytotoxicity of cyclopentadienyl ruthenium(II) complexes containing carbohydrate-derived ligands

“…The synthesis of ruthenium compounds bearing carbohydrate derived ligands is a relatively unexplored area: our bibliographic search revealed some examples of ruthenium carbonyl clusters containing carbohydrate moieties [30][31][32][33][34], ruthenium-arene complexes containing a carbohydrate phosphite derivative with anticancer properties [35][36][37], and a report of ruthenium cyclopentadienyl complexes with coordinated thiomonosaccharides concerning their promising anti-inflammatory effects [38].…”